


Forever Be My Always

by KissMeDeadly



Category: Gossip Girl (TV 2007)
Genre: Crossovers & Fandom Fusions, Dan Humphrey is Not Gossip Girl, Multi, Past Attempted Rape/Non-Con
Language: English
Status: In-Progress
Published: 2020-12-02
Updated: 2021-03-05
Packaged: 2021-03-09 20:41:02
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 7
Words: 12,506
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27832429
Author URL: https://archiveofourown.org/users/KissMeDeadly/pseuds/KissMeDeadly
Summary: Nobody, least of all Chuck, could have imagined how his life would change by being locked on that roof the night of the Masquerade Ball.
Relationships: Chuck Bass/Dan Humphrey
Comments: 7
Kudos: 13





	1. 10.24.08

**Author's Note:**

> See Notes at the end for Story Trivia. Also, special thanks to my friend and sounding board who's been with me for almost three years writing this story.

**Summary for the Chapter:**

> The night of the Masquerade Ball

Chuck was sitting behind the same column he’d been hidden behind when that bitch had stolen his clothes and locked him up here. He was planning the best way to figure out who the bitch was and how to utterly ruin her when he heard the door open. Finally, he thought, as he stood up as quickly and quietly as he could. He figured he’d wait until whoever moved out of sight of the door then head back into the hotel. From there, he could easily charm his way into the room Blair reserved for her plans with Nathaniel and call someone to bring him some new clothes. Nobody had to know some anonymous bitch got one over on him. 

Carefully he peeked around, only to completely forget his plans as he watched Serena get hot and heavy with Humphrey. He scoffed silently, wondering what she saw in the scholarship case of St. Jude’s. Still, he wasn’t gonna get any tonight and watching someone as hot as Serena was the next best thing. Pulling his gaze away from the action, his gaze swept over the expanse of the roof looking for a better view that would still be out of sight. Finding one, and figuring the participants of this show were sufficiently distracted, he moved. 

Comfortable and confident he was hidden from the lovebirds’ view, he turned his attention back to the show to find that they’d moved into second. He got a nice view of Serena’s boobs, as well as Humphrey’s surprisingly nice looking chest. He shook his head, where the hell did that thought come from? Focusing back on the two, he found that Serena had slid down Humphrey’s body. She undid Humphrey’s pants and pulled down his boxers giving Chuck a full frontal view of the other boy for a few minutes while she teased him before taking him into her mouth. 

Seeing Humphrey’s cock didn't faze Chuck, he’s seen other boys dicks before usually in locker rooms, but also he’d had glimpses of Nathaniel’s when he watched Serena take Nathaniel’s virginity at the Shepherd wedding and even once when he’d eagerly agreed when the girl he’d been seducing coyly asked if she could bring a friend. He thought she’d meant a girlfriend, turns out she meant her boyfriend. What did faze Chuck, as his body reacted to the live action porn he’s watching, is that he’s not paying as much attention to Serena as he is to Humphrey. 

What the fuck? Chuck’s eyes widened in horrified shock as that last observation actually registered in his brain. He closed his eyes, and pictured Serena blowing him. When his body reacted as he expected it to, he let out the breath he didn’t even realize he’d been holding and went back to watching. 

While he’s been having his minor sexuality crisis, the lovebirds had been busy. Serena was sitting in Humphrey’s lap, dress hiked up, riding the other boy for all she was worth. His hand went to his own hard cock, freeing it from his boxers. He hissed softly as heated flesh met cool October air. He wrapped his hand around himself and began to rub slowly. He tried to memorize the scene playing before him; Serena's head was thrown back as Humphrey sucked on an exposed nipple.

Instead, as he began to thrust into his fist, he found himself imagining that it was his nipple the other boy was sucking on. He forced his eyes open, to watch Humphrey's hand move under where Serena's dress was bunched up. The girl's loud imitation of a porn star told Chuck what Humphrey was doing. His eyes closed again, but instead of it being his hand playing with Serena's clit, it was him making those noises as Humphrey jerked his leaking cock. Feeling that he was close, he tried once more to focus on Serena, to think about how good it would feel to finally fuck the one pussy that eluded him. His imagination had other ideas though, and his body betrayed him once again as it tensed in release not to thoughts of fucking Serena, but to...

Confused and horrified as he was, he still had the presence of mind to bite his fist to muffle any noise he made. The last thing he wanted was for them to discover that they hadn’t been alone this whole time. Not because he actually cares if they know he watched them, his entire social circle knew he was a perv and he’s not about to start denying it now; but he won’t let that bitch who locked him up here without clothes humiliate him further by allowing his predicament to be known. 

He sat there, forcing himself to breathe as quietly as possible through coming down from a rather intense orgasm as well as the ensuing panic. He was Chuck Bass dammit!, and Chuck Bass was NOT interested in guys. Except, as his brain taunted him by replaying the mental image he’d apparently conjured right as he spilled into his hand; he had been in Serena’s place, taking the other boy's cock into his body. Viciously, he shut that line of thought down and told himself that he’d been thinking about Serena. Period. End of Story. Then calmly he tucked himself away and turned his attention back to where the lovebirds had been. 

Seeing that they were heading back inside, he sat back down content to wait long enough that it wouldn’t be likely he’d run into them figuring that they wouldn’t bother locking the door. After several minutes, as he was getting up to leave, the door opened again this time revealing Blair...holding a hotel robe. 

“Was she at least worth it?” Blair asked with a smirk. 

“What? What are you talking about Waldorf? And how did you know I was up here?” Chuck asked, Taking the robe. Blair just laughed as he pulled it on and tied it. 

“Let me guess, she got your phone too?” Chuck shot her an annoyed glare, however, Blair just smirked back at him. Finally, she continued, 

“It’s all over Gossip Girl, apparently some anonymous blonde was seen dumping your suit and mask down one of the hotel’s laundry shoots. I was just about to get into my car when the blast came. That hotel room isn’t being used for what it was booked for so I figured you could use it tonight and call Nate later today for your own clothes.” She gave him a long, intense look then without a word, handed him a keycard and turned to go back inside. 

He quickly headed to the room and let himself in. He was going to just take a shower and go to bed, worrying about getting his phone and some clothes in the morning until his brain decided to replay the show from the roof including the revelation he was resolutely ignoring changed his plans. Instead of heading straight to bed, he cleaned out the mini - bar. It wasn’t the expensive scotch he preferred but it would provide what he was looking for all the same...oblivion.

**Notes for the Chapter:**

> Trivia
> 
> * In this the Kiss on the Lips party (09.17.08), and the Masquerade Ball (10.24.08) happened senior year. Other timeline events are changed as well to fit what I wanted to do with them.  
> * Dan and Serena start dating on the Kiss on the Lips party  
> * Chapter titles are in the date format that Dan used as a title for the story he wrote about first meeting Serena in canon. The same story Vanessa had published in the New Yorker as a Xmas present.


	2. 10.31.08

**Summary for the Chapter:**

> Nate tries to figure out what has his best friend spiraling out of control.

**Notes for the Chapter:**

> *Text Message/Gossip Girl blast*

Nate knew he wasn't always the most perceptive person on the planet. Hell, according to Blair, sometimes he was just downright oblivious. But to be honest, he'd always thought Blair was just trying to nitpick him to her standards. As he reread the latest Gossip Girl blast, he thought maybe she had a point. 

*It has been an interesting week for Manhattan’s elite but none more so than C’s apparently. I've received tip after tip of C with a different girl, if not multiple girls, each day. Sleaze is nothing new, in fact, his reputation is nothing short of hard-earned but this is an all-time low. My faithful eyes and ears have also reported that C is rarely, if ever, sober anymore. Has C just spun completely out of control or is this a ploy to hide a much juicier secret…*

Nate knew he hadn’t been spending as much time with his best friend but he'd been caught up in his feelings for Serena, his guilt over hurting Blair and the annoyedjealoushurt that Serena didn't seem to be having any issues moving on. Not to mention the issues with his parents. Still, as he reread the blast once again, he decided he'd been a shitty friend long enough. Chuck was clearly dealing with his own issues, yet he'd still been there whenever Nate called. Shit, now he felt even worse. 

Decision made, Nate grabbed his jacket and keys before heading out the door to get a cab. During the ride over to the Palace, Nate scrolled through the last week of Gossip Girl for any other Chuck updates. There were a few, and it was pretty much all the same as the most recent one...reports of drugs, girls, and the inevitable fights Chuck always seemed to find himself in when he tried to seduce the wrong girl. Then he came across the blast about the girl who stolen Chuck's outfit from the Masked Ball. 

That had to be the start of it, in fact thinking about it, Nate remembered Chuck seemed to be acting weird when he arrived with the outfit Chuck had asked for. But wait, something was wrong with this picture, this wasn't the type of incident to inspire a binge at all; let alone one of this magnitude. No, usually Chuck would be plotting against the girl if he didn’t just let it go. So that wasn't the reason behind Chuck's madness, but whatever it happened the same night. That much was Nate was sure about, now he just had to get Chuck to actually reveal what exactly happened that night. 

Standing in front of Chuck’s door, he checked his phone for the time. Confirming it was late enough that last night's girls would be gone but early enough that Chuck wouldn't already be out; Nate let himself in. Having spent many nights crashing on the couch, he was easily able to navigate in the dark to the window which he pulled open letting light flood the room. 

“Nathaniel.” Chuck’s voice groaned from the bed, “Too bright.” He turned just in time to catch the pillow being thrown at him, as Chuck buried his head under another one. 

“What did you do last night?”Nate asked, setting the pillow at the foot of the bed. The other boy just groaned again, apparently realizing that Nate wasn’t going away. He waited until Chuck showed definitive signs of actually getting up before turning back toward the front of the suite. Knowing how Chuck was after a night like this, he got the shower started and ordered room service. After a few moments of thought, he called room service back and requested that their order is brought up by a male attendant. He needed Chuck to focus on him, not on hitting on the room service girl. 

The timing worked out perfectly, as breakfast was being rolled in just as Chuck came out of the shower in fresh clothes. Nate waited until Chuck fixed his coffee, sans the whiskey that Nate pulled from his hands before he could add a generous helping. He did hand him a couple Advil in exchange, figuring Chuck's head must be exploding. 

“Nathaniel,” Chuck complained, with a mildly annoyed glare. 

“Charles,” Nate said, mimicking his tone while holding his stare until the other boy rolled his eyes and took his pills with his coffee. He handed Chuck his chicken club, then dug into his own food. Not even a few minutes into eating, Chuck broke the silence.

“How can you eat that?” 

“Same way I can every time you ask that.” He laughed, Chuck was predictable when hungover. Once they finished eating, he set up the PlayStation then grabbed his best friend's pot stash. He needed Chuck to be relaxed and distracted, then hopefully he'd be able to get his best friend to confide what was messing with him. A few hours, and at least half of their pot later, he finally broached the topic. 

“So you never did tell me what happened the night of the Masked Ball…” 

“If you were aiming for subtle Nathaniel, you missed the mark by half a mile,” Chuck smirked. Nate laughed, 

“So subtle is more your and Blair’s forte,” he shrugged, “the question still stands.” 

“What question? I didn’t hear you ask one.” 

“Come on, Chuck. You know what I meant, you’ve been on a massive binge since the night of the Ball so what happened?” Nate said, giving up on any pretense of being subtle. Silence stretched several long moments, Chuck's jaw tensed then finally he nodded. Nate watched him carefully as he spoke softly and without inflection about asking the girl to dance, the game of hide and seek with a trail of clothes leading to the roof, and finally instead of getting the implied prize, he got locked on the roof in his under clothes. 

Nate studied his friend intently. He didn’t doubt everything Chuck said was the truth, he knew there was probably a long list of girls who’d been through this hotel room who’d enjoy setting Chuck up like that. However this wasn’t the whole story, Nate was sure about that. That girl should have been a minor annoyance, a reason to scheme, not this. Something major happened on that roof that he wasn’t saying. The fact that the normally unflappable Chuck Bass was all but squirming under his gaze proved that. 

“Man, that sucks.” He said, then leveled his best friend with his best imitation of Blair's unimpressed glare, “but that isn't what triggered the binge. 

“Nathaniel, please. That doesn't work on me when Blair does it, and your imitation pales in comparison.” He shrugged but pressed on, 

“Look, whatever is behind this overkill of drugs and sex, I know it isn't some random girl even if she did get one over on you. Quite frankly, I'm surprised you're giving her any more credit by laying this on her.” He waited and waited, as the silence stretched into an awkward level. Still, Chuck said nothing just stared at the screen, though he wasn't paying any more attention to the game than Nate, himself was. When the level of silence was nearing uncomfortable, Nate gave in. He rolled another joint and offered it to Chuck, a white flag of sorts. Chuck clearly wasn't going to talk, and continuing to push at this point would only make things harder. He needed reinforcement, and he knew exactly who to call, the one other person Chuck would confide in.


	3. 11.07.08

**Summary for the Chapter:**

> Chuck runs into some unexpected company at Victrola.

Chuck’s foot would not stop tapping though, from nervousness or excitement, he couldn't be sure. Hell, for all he knew it could be a symptom of the damn near cold turkey detox he'd put himself through. He’d cleaned up his act and was far more sober than he’d been for the majority of the past two weeks. In fact, the only thing he’d had today was a couple hits from a joint for nerves.

He glanced at his phone, then the door only to repeat the action a few minutes later when he didn't spot Blair. He’d invited her down to see the place as sort of one last test before he went to Bart with his idea to invest in the business. When Blair arrived, he led her to the table he’d reserved. Once they were seated, he inhaled deeply then spoke. When he'd finished his presentation, he waited for Blair's reaction.

“You want your father to invest in a glorified strip club,” She smirked, teasing him, “how Midtown.”

“Burlesque club,” he corrected, “a place where people are transported to a different time, somewhere respectable they can let loose without judgment. Pure…” His voice trailed off as his attention caught on the stage.

“Is that Humphrey? What's he doing here? More importantly, I wonder if Serena knows” Blair asked. There was a flash, and he pulled his attention away from where Humphrey was indeed standing on stage behind a folding chair to see Blair with her phone out, a pleased look on her face. Seeing her occupied, Chuck turned his attention back to the stage just as the speakers started blasting Ginuwine’s Pony.

His jaw went slack as Humphrey began to expertly move to the beat; his breath caught in his throat as the boy's hoodie came off leaving him in just a white undershirt and sweats. Chuck noticed the brunette that joined the boy on stage had to be at least ten years their senior otherwise, his attention never left his classmate. Something in his gut churned watching the two together. Before he had too much time to try and discern the cause, Humphrey was on his knees, thrusting his hips as he slid across the stage. Chuck swallowed hard, feeling the first stirring of arousal.

He squeezed his eyes shut, taking slow, even breaths. He hoped that would be enough to stop the unwanted reaction. When it seemed to work, he opened his eyes only to have to look away and clamp his mouth shut to keep any embarrassing noises from escaping as the arousal he'd just managed to abate came back tenfold. He tried not to watch the erotic scene before him, but he kept glancing back to the stage where Humphrey was straddling one leg of the brunette now sitting in the chair, and rolling his hips before he grabbed her head, thrusting her face toward his crotch. He tried to redirect his blood flow, but even the vilest image he could conjure didn't stop his body from reacting.

He heard Blair gasp, his heart rate racing at being discovered until he realized she had reacted to Humphrey doing a backflip off the chair. He forced himself to look more relaxed than he felt as he casually crossed his legs.

“See something you like?” A voice shocked him out of his thoughts. He froze, gaze dropping at the same time a knot filled his stomach.

“What?” Chuck snapped, as he turned to glare at the owner of the voice. The man in question is older, with long brown hair. He looks vaguely familiar, but he can't place it.

“On stage, you seemed enamored and your friend has been filming since shortly after my nephew and Leah came on.” The man gestured toward Humphrey and the brunette. Then turned to Blair,

“By the way, filming kind of frowned upon in here.” Quick as lightning, he had her phone.

“Hey.” Blair protested, “Give that back, who the hell do you think you are!?”

“Name’s Eliot, sweetheart, and I'll give it back once I'm sure that none of my dancers, my clientele or my nephew have to worry about this footage getting somewhere it shouldn't.” He said, handing it back as he finished speaking. Blair huffed, but then what the man said registered.

“Your clientele, that means…”

“That's right sweetheart, I'm the owner.” Those six words were the ice he needed to get his body to behave. He stood, turned and offered his hand.

“Mr. Spencer, I'm -” He was interrupted by the arrival of Humphrey and the brunette.

“Bass. Waldorf,” Humphrey greeted, awkwardly rubbing his neck. “What a surprise to see you here.”

“Not any more of a surprise than finding you here. Tell me, does Serena know what you're doing here?” Blair asked, in a tone which, regardless of her actual intentions, suggested nothing but genuine concern for her best friend.

“Friends of yours, Dan?” The brunette asked, keeping Humphrey from responding to Blair's accusation.

“Hardly.” Humphrey scoffed, “This is Blair Waldorf, Serena's best friend. And that's Chuck Bass, a classmate I, unfortunately, can't seem to avoid.

“Feeling’s mutual.” Chuck retorted, not liking the feeling that his words were a lie, or that he'd had to force them off his tongue. Not one to let things go, Blair asked again.

Does your girlfriend know what you're doing here...with this woman?”

“Leah is a family friend, and one of Uncle Eliot's newest dancers.” Blair started to speak, clearly not satisfied but he interrupted.

“Uncle Eliot?” He got a sour taste in his mouth as Humphrey smirked at him, brown eyes gleaming with amusement.

Eliot is Jenny and my mother's brother.” He turned to look at the man who had introduced himself as the owner to him and Blair earlier. His stomach dropped as he realized why the older man looked so familiar. Next to Humphrey's uncle stood another man, older with a mop of unruly dark hair and a stony expression.

“Dan, can you escort Miss Waldorf out? Eliot and I have some business to discuss with young Mr. Bass.” The unknown man said, deceptively calm. He nodded at Blair's concerned look, letting her know without words that she should go on. He knew she wanted to grill Humphrey who still hadn't answered her question, and he still hoped to invest in this club. This was just a bit of a twisted setback as far as he was concerned.

XOXO

Chuck stood stock still in front of Bart’s study, mentally going over his presentation one final time to calm his nerves. He opened the door, then stopped surprised to catch his father with Lily Van Der Woodsen in an intimate embrace. He smirked at Lily’s poorly attempted cover-up.

“Not much of an actress, is she?” He teased once Lily had left.

“You won't tell Serena about this…” Bart seemed to think for a moment, “you won't tell anybody about this. Lily wants this to play out in a certain way.”

“You're serious about her.” He couldn't hide the shock in his voice. His father had had a string of casual flings and one night stands for as long as he could remember but despite what a few of them wanted to believe, none of them had ever actually been a potential stepmother for him. He nodded, and Bart accepted it as he asked,

“What's with the business formal? Are you being arraigned for something?” He tried to shrug the comment off, with his reputation he knew his father tended to see the worst in him but that didn't keep it from hurting. Still, he pushed it down and started on his spiel. He was shocked yet again, but happy when Bart didn't reject his proposal out of hand and actually seemed to be interested in seeing Victrola. He quickly agreed to whatever time his father had available and left before his father could change his mind. He let himself smile when only a few minutes after he left, Bart texted him with an expected time.

XOXO

When Bart showed up, Chuck was sitting with Eliot and Nate watching as the brunette from earlier performed, thankfully without Humphrey.

“Chuck.”

“Father.” He greeted, then made the introductions. Both Nate and Eliot were open and affable, discussing the ins and outs of Victrola's day to day operation as well as other business matters with ease, despite Bart sitting arms crossed, and unspeaking. His expression went from stolid, to unimpressed, to downright scornful as Nate and Eliot’s relationship status came out.

“You expect me to invest thousands of dollars into an excuse for you to be around booze and...women?” Chuck flinched at Bart’s comment especially at the look he directed to Eliot and Nate during the hesitation in his words. Chuck stared down at the table, unable to look at either his father or the two men being treated so horrifically for who they loved, who they were attracted to. Then Bart turned on him, and with every word he fought the urge to curl in on himself.

Soon after Bart left, Chuck made his apologies and followed. In his car, he directed his drive to Malted, he had frequented several times during his recent binge. There was plenty of drug dealers peddling any number of substances, bartenders turned a blind eye to his age, and the girls were usually open to sex for money. Once he paid the cover, he headed to the bar. The bartender was a busty blonde whose name he never caught but had gone home with him early in the parade of girls he used to try to convince himself he was straight. She offers him a flirty smile, to which he shook his head. He's not really interested in taking anybody home tonight, and even if he was, he'd already slept with her. He wasn't prone to repeats. She shrugged, offered a more friendly smile and asked,

“Glencallan, double on the rocks?” He blinks, not having expected her to remember his usual order. He hadn't thought he was that much of a regular for that. He shook his head slightly, and said,

“Straight.” She nodded and turned to pour his drink. Once he had it in hand, he laid a couple hundred dollar bills on the bar and tilted his head toward his normal table. She nodded again, and he knew she understood his nonverbal request to keep them coming. He glanced around the room then, deciding alcohol was enough, headed toward his seat.

Chuck was well on his way to drunk when the thrum of a familiar song came on. His eyes drifted closed, the memory of Humphrey on stage wasn't dulled at all by the haze of alcohol. He forced himself to open his eyes with a shake of his head. He stood, and made his way to the door; a bit wobbly but able to walk on his own.

Still feeling the effects of the two doubles he'd imbibed at the bar, he decided he'd have one more drink though he'd savour this one.

_Chuck sprawled out in his usual booth, watching the dancers when suddenly the entire club goes dark. When he can see again, he's sitting in a chair on stage as the familiar thrum of Ginuwine's Pony began to spill from the speakers. There was a whisper of breath in his ear,_

_“Did you enjoy watching me?” He shivered as the lights came up and Daniel moved out from behind him; shirtless, hips swaying in a way that had Chuck's eyes following his every move. His breath caught when Daniel teasingly removed his sweats. The boy, now left in nothing but tight black briefs, worked his body to the floor where he spun to face Chuck._

_He swallowed hard, his body reacting to Daniel pulling his body across the stage, thrusting his hips as he moved. Daniel stopped less than a foot in front of him and pushed his body into a handstand. Chuck's body flushed with growing arousal; the other boy opened his legs into a full split giving Chuck a full view of a hard cock encased in black fabric. He shuddered, his arousal spiking with the thought that Daniel was just as affected by this as he was._

_Then Daniel bent, giving Chuck an equally nice view of his ass before it landed on his knees. He let out a shaky breath as nice and slow, the other boy slid up his thigh providing the first tease of friction to his achingly neglected cock. Daniel, now fully in his lap, rolled his hips while trailing Chuck’s hands up Daniel's body from his knees to his hips. His hands clenched, hard enough to bruise when Daniel twists; only to move to help support the -- very flexible -- boy, as he pulls one leg up and twists again so when he puts his leg down again he's straddling Chuck's lap._

_Harsh breath interspersed with moans filled the air as Daniel settled into a rhythm: grind, roll, and repeat. He teetered right on the edge, needing just a little more. His eyes opened when Daniel paused, and he found himself staring right into bittersweet chocolate eyes. The owner of said eyes held contact with his own as he began again, a much slower and more deliberate pace that had him gasping and shuddering but still wasn't quite enough. Until Daniel leaned in, close enough that their breath mingled, and whispered_

_“Come for me, Chuck.”_

Chuck's eyes popped open just as his body tensed with his release. He laid there, breathing heavily and trembling from the intensity of it. Once his breath evened out, his eyes closed again as he growled,

“Fuck!” After two weeks of near constant inebriation and as many girls as he could pick up, he'd almost convinced himself that he had been watching Serena on that roof. Even his reaction at Victrola's could have been to the woman on stage - nevermind that he'd barely looked at her - but this? He hadn't had a wet dream since he first realized that being who he was could get him pretty much any girl he wanted, any time he wanted. And now, he was having one about Humphrey giving him a lap dance. He came, albeit subconsciously to the thought of Humphrey.

He grimaced in distaste, both at the idea and at the proof that it happened that was quickly making him uncomfortable. He got up and made his way to his bathroom where he quickly shed his soiled clothes and started the shower, running the water as hot as he could stand it. Stepping under the spray, he let his thoughts wander. Much to his chagrin, they turned to the fact that despite what he wanted to believe, his orgasm on that roof had absolutely nothing to do with Serena, just like his arousal at Victrola had nothing to do with the woman on stage. And the dream he'd just woken from…even having cum, the thought had his cock twitching with interest.

He wasn't gay, he'd never had any issues sleeping with the girls he seduced. So he was bisexual. In of itself, that didn't bother him. He cringed at the idea of his dad finding out though.

**Notes for the Chapter:**

> Trivia
> 
> \- Eliot Spencer, Nate Ford, and Leah Hart, an alias for Ashley Moore are all from TNT"s Leverage.  
> \- Eliot being the Humphrey children's maternal uncle is from an abandoned fic that I never posted.  
> \- For anybody familiar with Leverage, this is set post series where Nate retired with Eliot (my OTP) while Sophie is still  
> working part time with Leverage. In fact, though only Ashley is seen, the rest of the crew is there working a job.  
> \- For anyone interested in Dan and Ashley's dance routine, it can be found at [ Magic Mike Routine ](https://www.youtube.com/watch?v=tQSgOJOZwiw&t=4s)


	4. 11.14-15.08

**Summary for the Chapter:**

> On Blair's birthday, she and Nate finally get to the bottom of Chuck's downward spiral.

For Blair, tomorrow is the day every teen eagerly awaits; tomorrow she is legally an adult. However, it's not the happy occasion she always thought her ascent into adulthood would be. She'd always envisioned that she and Serena would rule their senior year together, that she and Nate would be at least happily headed toward, if not already engaged and she'd get her much worked for acceptance letter from Yale. Her dreams for college may still be on track, but everything else was in shambles. She and Serena were tentatively rebuilding their broken friendship, her relationship with Nate was barely hanging on by a thread. On top of everything else Chuck, the only other person she considered an actual friend, had been weird lately. 

There was nothing she could do about Serena or Nate at the moment, it would take time to fix what was broken. So, she decided, she'd focus on Chuck. Besides, since Nate had come to her for help concerning Chuck’s recent mega spiral she could probably kill two birds with one stone. She texted Nate to meet her in Central Park in an hour by the pond. Once she had his confirmation, she started to get ready. 

At the pond, she immediately spotted Nate. He was standing where he usually did when he beat her here. 

“Hey.” She called, getting his attention. He turned to her, and smiled. Her heart fluttered but she ignored it. This wasn't about them. 

“Hey, you said it was important?” He asked.

She nodded, “I've got an update on what you asked me about last week, but first has he told you anything about what happened with his dad and Victrola?” 

“He said Bart wasn't impressed, but was really tight lipped about any particular reason why.” Nate informed her. 

“But he bought Chuck the shares anyway?” She asked, puzzled. This wasn't like Bart; for all that Chuck was spoiled, it wasn't because his father went out of his way to do so. 

“All he said was somebody close to Bart said they'd talk to him for Chuck. Whatever this person said clearly got through.” Nate shrugged. Though her curiosity was piqued, Blair let it go. Instead, she filled Nate in on what Serena had confessed to her. 

“So Chuck most likely watched Dan and Serena,” Nate stated, clearly thinking. “Chuck’s my best friend, but we all know he's been a perv since puberty and he's wanted Serena forever. She's the only girl that's ever turned him down. He even admitted to watching Serena with…” Nate trailed off but she continued, 

“...With you.” She didn't like the reminder of Nate and Serena’s betrayal but it couldn't continue to be an eggshell topic if they were going to get past it. Besides, as Blair reminded herself yet again, this wasn't about them. 

“An opportunity to watch Serena wouldn't have had this affect on him. If anything, he'd be more smarmy than usual rubbing the free show he got in Serena’s face.” 

“I know, it doesn't make any sense.” She agreed, thinking through what limited information she had, “Unless...but no that doesn't make sense either…” She mused more to herself. 

“What?” Nate asked.

“Did Chuck tell you what happened when I met him at Victrola?” Blair asked. Nate shook his head, 

“Not a word.” 

“Humphrey was there -- on stage, dancing with another woman.” 

“Dan...Dan was onstage at a burlesque club. Does Serena know?” Nate asked, shocked.

“No, he claimed that he was learning the routine to help his uncle”s newest dancer.” She wasn't sure how much she believed that, but whether Humphrey was faithful was a concern for another day. “Anyway, the point is while Chuck thought I was too occupied filming, he never took his eyes off the stage.”

“So, he was interested in the dancer.” Nate said, tone clear that he didn't get what she was implying. 

“You would think so but Chuck was trying to hide his reactions, like he was embarrassed or afraid to be caught. Plus, when Humphrey introduced her he barely even acknowledged her.” 

“So you think he was watching Dan, both times?” Nate asked. She allowed herself to shrug. 

“He's the only thing that both incidents have in common.” She said, then checked her phone for the time, “I've got to go, but I'll see you at the party tonight…” Her voice raised slightly on tonight, making it a question. 

“Of course.” 

XOXO

Twelve o’ one am, she stood with Nate on one side of her, and Serena on the other as she closed her eyes to make her birthday wish...please let everything work out between Nate, Serena and herself. She opened her eyes as she blew out the candles. They had cake,and drinks, she opened presents, and everybody generally had a good time until it finally started winding down close to two in the morning. 

She waited until Serena left with Humphrey and Abrams before she caught Nate's gaze with her own and gestured toward Chuck. It seemed as though Nate understood as he caught up with the inebriated boy. Blair quickly grabbed what they needed and headed in their direction, catching up just in time to see Nate climbing into the Bass limo. She quickly climbed in and spoke to the driver, 

“We're going to the Palace.” The ride was comfortably silent though Blair could tell Chuck was suspicious of what was going on. When they made it to the suite, Chuck immediately went for his bar. While he poured himself a drink of his preferred Scotch, Blair set up the leftover sake and sushi from her party. 

“I know why you're both here.” Chuck stated. 

“Good, then you know you're not getting out of it.” Blair retorted. She'd spent more of her party than she cared to think about watching Chuck, and his reaction to Humphrey. He seemed to have been torn between avoiding Serena's boyfriend like a plague, and getting as close as he could without anybody catching on. 

“We're your friends, Chuck, we're concerned about you.” Nate said. 

“I'm not nearly drunk enough for this.” Chuck muttered, though not softly enough to not be heard. 

“Well then drink up, because we're not leaving until you talk to us.” Blair said. Several minutes passed where nobody spoke, though Chuck continued to down scotch like it was water. Finally her patience wore thin; she snatched the glass out of his hand.

“We didn't come here to sit back and watch you drink yourself into oblivion.” Blair snapped. Chuck offered her a weak smirk; admitting without words that, that was exactly what he'd hoped they'd do. 

“Come on man, whatever it is you can tell us. We won't judge, we're your friends.”

“Right,” Chuck scoffed, “because we never judge each other.” Blair dipped her head as she conceded the point,

“Okay maybe we do sometimes, but we always come together when it really matters.” She said, as she handed his glass back to him. “How about we start off easy, what happened with your father at Victrola?”

“Bart wasn't exactly impressed, but he seemed open to listening until he realized that Eliot and Nate aren't just business partners or friends. I've never seen a business meeting turn that hostile, so quickly.” Chuck answered; as he got up to refill his drink he muttered, “Bart's gonna kill me if he ever finds out, or worse disown me.” 

“Your father wouldn't do that.” Nate tried to sound reassuring. She was quiet though, she was certain now that she was onto something with her theory. Given what Bart let him get away with, there was only one thing that would ever have Chuck worried about being disowned. 

“Wouldn't he, it's not like he likes me as it is, finding out that his own son…” Chuck went silent. Blair heard what he couldn't bring himself to admit out loud, this downward spiral was Chuck having a sexuality crisis. It wasn't a secret among their circle that Bass senior was a homophobic ass; coming out, even as bisexual, would turn his entire life upside down. 

Blair moved to sit next to her clearly distressed friend, giving in to the urge to wrap him in a hug. She caught Nate's eyes, worried when all Chuck did was lean into her. 

“Well, you know none of us are going to judge you for liking boys.” She said, feeling him tense at her vocalization of the words he couldn't say. “You realize, though, that Serena isn't going to be happy if she finds out you want to sleep with her boyfriend.” Chuck jerked away from her, twisting to face her with an almost comical expression like she'd sprouted another head. 

“What would make you think I'd want to sleep with Humphrey. I may be interested in sleeping with other boys but I still have standards.” Blair bit her cheek, trying to keep from laughing. Nate, however, either didn't bother trying or couldn't prevent his from escaping as he said, 

“Man, your standards were breathing, reasonably attractive and female -- and the last one only partially applies anymore.” 

“So?” Chuck asked, his tone was disinterested but Blair could tell it was forced. 

“So, Dan is breathing.” Nate pointed out. 

“And he was certainly attractive enough for you on stage at Victrola.” Blair added, a knowing smile gracing her mouth, “considering you were...what was the word Eliot used...enamoured.” She spoke to Nate. “More like turned on, you should have seen Chuck during Humphrey's performance -- regulating his breathing, his Adam's apple bobbing and of course, the discreet leg cross.” 

“Come now Waldorf, I thought you were smarter than that. I was watching Leah.” Chuck argued. She laughed then, only to laugh harder when he glared at her. 

“You don't honestly expect me to believe that do you, Bass?” His expression, the epitome of 'if looks could kill’, had her biting her cheek to keep from laughing again.

“Okay, you were watching Leah.” She conceded,then deciding she wasn't going to humour him after all, asked innocently,

“So what was she wearing?” Chuck looked at her, puzzled. 

“Who?” 

“Leah. If she was who you were watching so intently, then you should know what she was wearing.” Blair clarified.

“She…”Chuck paused, then after several long moments, said, “I don't remember.” 

She wasn't surprised, but now she had proof. Chuck hadn't paid the slightest attention to Leah Hart. What did surprise her was the defensiveness in his voice. That caused her to drop the subject, but also piqued her curiosity. Chuck rarely got defensive, and never about the people with whom he wanted to have sex which she was now without a doubt sure included Humphrey. Except he was…and she couldn't put her finger on why.

**Notes for the Chapter:**

> Trivia
> 
> For those of you who spotted it, yes there is a Harry Potter Easter egg in this chapter.


	5. 11.22.08

**Summary for the Chapter:**

> Chuck's testing of his new found sexual orientation at a gay bar doesn't go as planned.

Chuck stepped out of the taxi and glanced around. Not seeing anyone paying him any attention, he quickly made his way inside. Immediately after hanging up his coat, he headed to the bar. Getting the bartender's attention, he ordered his usual Glencallan 18 on the rocks. He gave a quick once over to the bartender, a slender redhead. With a shake of his head, he offered a friendly smile as he paid for his drink, and left the bar. His entire purpose to this risky endeavor was to go home with someone of his own gender. 

He settled into an empty table near the stage and sipped his drink. The bar was fairly crowded; people drinking, dancing, and playing pool. Several drag queens worked the room, mingling and getting their pictures taken with people. Soon though, the music died down and the DJ came over the speakers. 

“Hey, boys, girls and all in between, Y'all ready to get this party started!?” The crowd went wild, and so the DJ continued; he introduced himself then went on, 

“Let's hear it for our Metro - sensual dancers tonight! Richie Martin! Juan Diesel! Chase Kilos! Ty Mozart! And for our lady-loving ladies, we've got Ashlyn Ryan and Desiree Storm.” Chuck gave each of the four well built, very fit men a once over as they came out in nothing but form-fitting underwear from backstage only to frown as the crowd went wild. All the guys were attractive but in the same sense that a straight guy would have acknowledged. There was no arousal, none of his body’s reactions to someone he wanted. Not to the men anyway, checking out the female dancers, he reacted as he expected to. It didn't make any sense, his body reacted to Humphrey almost instantaneously. It was almost enough to make him think maybe he was straight, after all, but the wet dream didn't feature anyone but him and Humphrey. Actually, as much as he hated to even think it, Humphrey had starred in most of his erotic dreams recently. 

He let out a breath as he tried to make sense of what the hell was going on with him. He debated just getting up and leaving. Whatever this was didn't seem like it was going to impair his sex life too much so he could just ignore it, go on as before…

“You don't look like you're having a good time, maybe I can fix that?” A voice asked, pulling him from his thoughts. He looked over to see one of the male dancers, giving him a very familiar look. On the other hand, he already took the risk of coming out to this club, might as well at least do what he came for. He offered the guy a seductive smile, 

“What exactly do you propose?” He asked. 

“Dance with me?” The guy suggested, holding a hand out. Chuck nodded, then stood and followed the guy out to the dance floor. His hands held the guy's hips as he ground his ass against Chuck's crotch. Soon, his dance partner had turned in his arms and joined their mouths together. As it turned out kissing another guy wasn't much different than kissing a girl. They made out as they danced until the need for air pushed them apart. 

“Follow me.” The guy whispered though he didn't actually wait for a response before he was being pulled along. They came up to a door that read, Private. 

“This is the dancers dressing room, technically you're not supposed to be back here.” The guy whispered. 

“I won't tell.” He responded before reclaiming the guy’s lips. Eventually, they found their way to a couch. He was pushed down, then the guy was straddling his lap and his hands were pulling his shirt out from his waistband. He felt warm fingers roaming as much skin as he could reach. His own hands moved instinctively to his partner’s hips, resting there but not restrictive. 

His partner groaned and thrust against him, causing him to freeze as their erections came into clothed contact for the first time. It seemed his awkwardness didn't go unnoticed. 

“Everything okay?” He nodded; mentally rolling his eyes at his own ridiculousness. He was Chuck Bass, and if there was one thing he knew it was sex. This may be his first time with a guy but he did not panic like the nervous virgin. Besides, it wasn't like he had any plans of bottoming and anal sex with another guy couldn't be that different from anal with a woman. 

He turned his attention back to his partner who was kissing along his jaw, fingers working his shirt open. His own hands trailed up along the warm, smooth skin of the man in his lap. Then he felt the other man's hands on his belt. He tried to fight against the heaviness he felt in the pit of his stomach, but his body tensed nonetheless. 

“Wait.” He shook his head, “I can't do this.” 

“Things were fine just a few minutes ago…” The guy said

“And now they're not.” Chuck snapped. 

“Okay.” The guy agreed his hands up in surrender, moving off his lap. He stood up and reached for his wallet. He pulled out some fifties, not even bothering to count them, and pressed them into the dancer’s hand then left without looking back. He stopped to get his coat, then he was headed toward the street where he hailed a taxi. 

They hit traffic, despite it being after midnight so it took about forty-five minutes to get back to the Upper East Side. He spent that time trying to bury this incident as far into the recesses of his mind as he could. He'd never… no, he wasn't thinking about this. Finally, the taxi pulled up outside the Palace. He paid his fare and headed inside. All he wanted when he unlocked his door was to put a major dent in the stock of his wet bar, and forget about tonight. Unfortunately, as soon as he entered his suite, he could hear what sounded like Grand Theft Auto and smelled pot smoke. 

“Hey man, where have you been?” Nathaniel asked. 

“Don't you have your own game console?!” He snapped. The room fell painfully silent. He huffed in frustration and counted to ten… in Russian; something Laryssa had taught him. Nathaniel had nothing to do with what had him in such a mood, and he really shouldn't have taken it out on him. He poured himself the drink he wanted, then he poured one for Nathaniel.

“I really just don't want to talk about it.” He said, letting his regret at the way he'd snapped before come through his tone. He held the drink out to his best friend, “Can we just play a few rounds, smoke and not think for a while?” Thankfully, Nathaniel stayed true to form. He took the proffered drink, and handed him a controller.

**Notes for the Chapter:**

> Trivia
> 
> -Laryssa is Chuck's former nanny turned maid taken from the web series Chasing Dorota which can be found on Youtube.


	6. 11.27.08

**Summary for the Chapter:**

> Friendsgiving at Narcissa.

Serena re-entered the Humphrey loft, Blair in tow to find what had been a lively, if slightly awkward affair had turned to much more awkward tension featuring just her mother and Rufus. They stood there for several excruciatingly long moments, not wanting to interrupt whatever this was until Rufus seemed to realize they were there. 

“Dan’s room.” She nodded in silent thanks, and led Blair to where Dan, Jenny, and Eric were holed up. 

“Serena, you're back.” Dan announced, “...and you brought Blair.” 

“I hope you don't mind.” She said, pressing a kiss to his mouth. 

“No, of course I don't mind. She can hide in here with the rest of us until the extremely embarrassing parental awkwardness dissipated which may be some time around New Year.” Dan quipped. 

“Speaking of, why is everybody hiding in here?” Serena asked. 

“It turns out your mom and my dad dated at some point before they married your dad and my mom.” Dan explained. 

“But we've determined that we're not related.” Eric added. 

“I don't know,” Jenny teased, ruffling Eric’s hair, “your roots are kind of Rufus-like.” 

“So our parents…” 

“Well, we didn’t stick around and ask for details but we're thinking it's safe to assume.”Jenny quipped. She and Dan blanched at the same time. 

“And here I thought my family was insane.” Blair commented, then “Ooh, is that Cedric?”

“Just when I thought this day couldn't get any worse.” Dan complained. 

“This is too much to deal with on an empty stomach, can we get out of here?” Serena asked. 

“Yeah sure, we'll take the fire escape.” Dan said, as he opened his bedroom window. 

“Is anything even open?” Eric asked. That stopped everybody in their tracks. They all looked at each other. A moment later, Jenny shook herself out of the stupor they'd all fallen into and went for her brother's laptop. The room was silent except for the clicking of keys until she read, 

“There's a list of twenty-two restaurants that aren't only open today but offering Thanksgiving themed menus.” The list was read out loud, with them quickly vetoing several until they finally decided on Narcissa. Once they'd climbed down to street level and gotten a town car large enough for the five of them, Serena had an idea.

“B, why don't you see if Nate wants to escape yet.” She suggested. A few minutes of texting back and forth occurred before Blair said,

“Apparently he already has, he's at the Palace with Chuck. I invited them both.” Serena shared a look with Dan as she said, 

“That's great.”

XOXO

At the restaurant, they found the boys waiting for them as they were closer at the Palace than the rest of them coming from Brooklyn. Serena gave her name at the hostess station and they were immediately shown to a large circular table where the staff carried a couple more chairs over. 

Dan pulled her chair out, then sat to her right. She watched puzzled as Blair quickly put a hand on the back of the next two chairs to Dan’s right forcing Jenny and Eric to take the seats to Serena’s left. Her confusion worsened when Blair took the second chair, then patting the chair to her right.

“Nate, why don't you sit here?” Blair asked. Serena frowned. Blair had just maneuvered their sitting arrangements so Dan and Chuck would be sitting next to each other, but why? Of course, Blair didn't know that having Chuck here with both Dan and Jenny was a clusterfuck waiting to happen but Serena knew Blair had seen the animosity between the two boys. She sent up a silent prayer that Chuck would behave for the hour or so they'd be here before turning her attention back to the boy in question. The dirty look Chuck sent Blair wasn't unexpected, but the widening of Chuck’s eyes when he looked back toward the chair next to Dan as he stood there playing with his scarf shocked Serena. She glanced back at Blair to see her smirking at him. 

“Come on Chuck, don't just stand there come sit down so we can order.” Blair said, not bothering to look up from her menu. 

“Blair.” Nate chided, clearly aware of whatever was going on. 

“It's fine Nathaniel,” Chuck drawled, “Blair can play her little game.” Serena’s gaze shifted between her three oldest friends; what game was Blair playing with Chuck and what did it have to do with her boyfriend. Once the waiter had come, and left with their orders, Nate broke the silence.

“So Blair, how was seeing your dad? It's the first time since he left right? I'm kind of surprised you’re here.” 

“I don't want to talk about it.” Blair said. 

“Eleanor disinvited him then told Blair he canceled due to being too busy with his boyfriend.” Serena said, ignoring the glare being sent her way, “You’ve already relapsed once today, bottling it up will only make it worse.” 

“I’m fine Serena, so my dad didn’t show. At least I didn't find out my boyfriend could have just as easily been my brother.” Blair snapped. 

“Wait...what?” Nate gaped. 

“My mom and Dan’s dad used to date. Now please, can we not mention this ever again?” Serena shuddered. Thankfully, the wait staff choose that moment to bring out the food. Conversation ceased as everybody's attention turned to their food. 

After a few minutes of digging in, Blair introduced the next topic. 

“Little J, are you interested in helping me with another event? 

“Yes, I'd be happy to.” Jenny excitedly accepted. 

“You're planning a new event B?” Serena asked. 

“Yes, a benefit for a local organization for LGBT teens.” Blair said, with a mischievous look. Serena followed her gaze, to find Chuck wearing an odd expression though it disappeared in the blink of an eye. Then Dan jumped in,

“Have you picked an organization yet?” He inquired. 

“Not yet.” Blair admitted, “though I've checked out a few that have potential.” Dan asked her about which ones she was considering, and next thing Serena knew Dan and Blair were discussing the various LGBT teen charities of Manhattan. She smiled at her boyfriend and her best friend finally finding some common ground. She went to engage in her own conversation, but movement drew her attention back toward Dan and Blair. 

Chuck was leaning forward, his body ever so slightly angled toward Dan. Though he looked kind of annoyed, he was paying apt attention to a conversation he wasn't actually taking part in. Something in Chuck’s behavior was weird but as she couldn't put her finger on it she opted to ignore it. She turned her attention to the conversation going on between Nate, her brother, and Jenny about college. 

“I just don't want to go to Dartmouth.” Nate said, “Or any Ivy, I'm really looking at schools on the West Coast.” 

“There's a really prestigious fashion design school out there in LA, I just have to get in.” Jenny said. 

“Why wouldn't you get in, you're at the top of our class.” Eric said. 

“I have the grades yeah, but I need something that'll really help me stand out.” 

“I think I want to --” She stopped when from the corner of her vision she saw Chuck signal for the waiter. She looked over in time to hear Chuck ask, 

“Can we get a refill?” She was about to turn back to her conversation when she noticed Chuck didn't need a refill, nor did Blair. Then she noticed the empty glass in front of Dan. She frowned, then shrugged it off as part of whatever weirdness had Chuck in its clutches. She turned back to see Jenny looking in her brother's direction with a weird expression. Before she could question Jenny, Nate was answering his phone, 

“Hey Mom, I'm… He what?! Is he gonna be okay? What hospital are you going to? I'll be there as soon as I can. Yeah, I'm leaving now.” Conversation ceased as Nate’s side of the call was heard. 

“Nate?” Blair inquired softly, laying a hand on his arm. 

“My dad, he- he overdosed. He's at Lenox Hill Hospital. I've got to go..” Nate admitted, as he looked around for a waiter. Immediately those at the table sprung into action; Blair got a waiter’s attention and handled the various bills while Serena led Nate outside where they flagged down a cab. When she came back in, she approached Dan, Jenny, and her brother.

“I'm going to go with Blair, but I'll get you a cab back to the loft.” She said. 

“Don't worry about it.” Chuck cut in before they could respond, “I've already arranged a ride for them.” She nodded then went back to where Blair was waiting for her own cab. The others came out a few minutes later, and she frowned when Chuck spoke to her brother before coming over to join them. Their car pulled up, and once they'd all piled in she asked, 

“Why are you here?” Chuck looked at her strangely, 

“Nathaniel is my best friend, why wouldn't I go?” She shook her head, 

“I mean, why aren't you taking your limo?” 

“Mikha is dropping Eric off then taking your boyfriend and his sister back to Brooklyn.” She frowned. Chuck was being very nonchalant about something majorly out of character for him. He may offer someone a ride if he wanted something from them, but never had he let someone borrow his driver. This on top of all the other weird occurances made her ask, 

“What are you two up to?” 

“I don't know what you're talking about.” Chuck said. Her eyes narrowed, trying to play dumb wasn't a good choice. Her mouth opened, but Blair cut her off. 

“Considering the circumstances, now isn't the time for this S.” That stopped her short, especially as they'd just pulled to a stop in front of the hospital. She and B got out as Chuck paid the driver, then they all headed in to find Nate.

**Notes for the Chapter:**

> Trivia
> 
> \- Narcissa is the name of a real restaurant in NYC.


	7. 12.19.08

**Summary for the Chapter:**

> Blair hosts a Rocky Horror Picture Show themed benefit for LGBTQ youth, and Chuck finally has his first time with another guy.

_Chuck was watching Daniel and Serena, hard cock in hand working himself to orgasm when a hand grabbed his wrist. He looked up to see Daniel smirking at him, Serena still riding his cock. He looked back at Daniel with a hiss as he felt Daniel's hand replace his own on his cock and began to stroke him. Unlike his hurried, don't want to get caught pace, Daniel's hand moved achingly slow._

_"Did you enjoy the show Chuck, did you get off watching Dan fuck me? I bet you did, but it wasn't me you were thinking about was it?" Serena asked, slowing her pace and he found his gaze drawn to where the two were joined. His muscles clenched, and he shivered at seeing her body stretch to accommodate the other boy's cock. "No, it was his thick, hard dick. You were picturing how good it would feel to be stretched open and fucked."_

_Suddenly, he was laying down on something far softer than that roof had been; completely naked with an equally naked Daniel kneeling between his legs. He groaned as Daniel's hand continued to stroke his cock, just firm enough to keep him on the brink of release. He felt Daniel trail his fingers from his hip down along the line of his inner thigh... a gasp escaped him as the exploring hand found his balls. Then suddenly slick fingers moved lower, then progressively lower with each stroke until Daniel was teasing his taint and hole. He just teased over and around his rim, never trying to breech him. He squirmed, pushing back trying to beg for more pressure without words._

_"That's it, show him what you want.”_

_“Daniel, please!” He finally gave in and begged as it seemed Daniel would never give him enough pressure to cum. He was so close when he heard his name, but it wasn’t Daniel…_

_***_

Chuck!” He blinked owlishly as awareness came to him. His gaze darted around the room before he realized Da - Humphrey, he mentally corrected himself - had never been there. Instead, Nathaniel was standing by the foot of the bed smirking at him.

“Good dream?” His best friend asked, “About a certain Brooklynite we know perhaps?”

“Don't make me sick Nathaniel.” Chuck scoffed, grimacing as he became aware just how close he'd been to having another wet dream...in front of his best friend. His eyes closed, he focused on willing his erection away. Frustration swirled at his body's refusal to cooperate. He wasn't attracted to Humphrey, he refused to be. He could deal with being attracted to men, but Humphrey? He didn't like the self-righteous social climber, dammit! His brain knew that, so why couldn't his body figure it out?

“Yeah, I might believe that...if I hadn't just heard you call out ‘Daniel, please!’ during what was clearly a sex dream. So Blair was right, you have a thing for him?” Nathaniel continued to smirk at him.

“I do not have a thing for Humphrey. And stop smirking at me, it doesn't suit you.” Chuck snapped, annoyed and embarrassed. Now his best friend knew he was having erotic dreams featuring Humphrey, that was bad enough but he’d heard Chuck reduced to begging. He resisted the urge to bury his face in his hands or pull the cover over his head and refuse to come out. He was never going to hear the end of this, and he didn’t even want to think about when Nathaniel told Blair -- because he would.

“Methinks someone doth protest too much.” Nathaniel teased.

“Remind me why I let you crash here?” Chuck asked, getting up and pulling his robe on.

“Because I'm your best friend, and as such it's my job to rag on you especially when I wake you up from a sex dream about one of our guy friends.” Chuck scoffed,

“Humphrey is not my friend.”

“I guess he isn't… I mean he's made no secret of the fact he doesn't like you. However, I noticed you didn't even try to deny the dream was about him.” Nathaniel pointed out. He scowled at his soon to be ex best friend as something inside him clenched painfully at the reminder that Humphrey didn't like him. Then his ire changed focus, why did he care whether Humphrey liked him or not. He did not have a thing for the other boy.

“Why waste my breath denying it, you're clearly set in your delusions.”

“Or maybe you're not denying it because you know, we both know it's true.” Nathaniel pointed out. His jaw tensed, he wanted to deny it, hell he wanted to not need to deny it. However, the more he tried, the more his mind and body betrayed him. Images and words from the dreams were a constant reminder that as much as he hated it, Humphrey was the focus of these dreams and the arousal and/or release he got from them. Not that he'd ever say that out loud, especially to his friends or God forbid, the boy in question. Still, he knew he had to give Nathaniel something if he wanted this subject to drop, which he did. Desperately. Finally, he nodded.

“Fine, Serena’s charity case may have made an appearance but it wasn’t pleasant and it's definitely not a thing.”

“I don't know, he must have been doing something right to make you beg.” Nathaniel laughed, He shot a dark look toward the other boy.

“Shut up.” Chuck demanded, heading toward the bathroom to get ready for the day.

XOXO

He entered the venue with a group of other guests, to see actors dressed as Riff Raff and Magenta standing in what had been decorated to resemble the entrance to Dr. Frank N Furter’s mansion. When the opening chords of Time Warp started, Riff Raff and Magenta performed as the group walked through into the main ballroom just as they had in the original movie.

Once inside, there were actors scattered throughout the crowd who continued the performance and were teaching the guests how to do the Time Warp. He headed toward the bar; then with a drink in hand, he went looking for the hostess.

He found her with Serena and Humphrey. He greeted Blair first, offering a compliment on how good the party turned out. Then his attention turned to Serena. His eyes slid up and down her form, as was his habit. The slinky dress she wore didn't disappoint but while he still wanted her, the desire had dulled considerably. Finally he offered a clipped greeting to Humphrey and turned his attention back to Blair before he accidentally gave in to the urge to check out his body like he had Serena's a few moments previously. Unfortunately that meant he caught the calculating look in Blair's eyes before she took Serena's arm.

"Come on S, I wanted to talk to you about something." She said, dragging the blonde away. He watched the two girls disappear into the crowd, wondering if Blair really thought that was even remotely subtle. Once they were gone, he found his gaze returned to Humphrey. The other boy was staring in the direction that the girls had disappeared, lips turned down into a frown and arms crossed. Of their own accord, he crossed his arms over his chest as well. Realizing he had mirrored the other boy, he uncrossed his arms and forced his gaze away only for it to return moments later. Despite his earlier desire to avoid doing it, he found his gaze sliding over the other boy's body. He tried to focus on the negative aspects, to remind himself why the Brooklynite wasn't worth all the frustration he was causing.

That didn't work as well as he had hoped it would. While the cheapest part of his own outfit was more expensive than everything Humphrey was wearing put together, it didn't actually look bad on him. He forcefully stomped on that train of thought, stopping it in its tracks. He didn't want to think about how good the other boy looked despite the cheap clothes, or about how he looked out of them. Quickly downing his drink, he found himself breaking the awkward silence.

"I need another drink, want one?" He felt his own eyes widen, shocked at the words that had left his mouth without his permission. Humphrey didn't seem much better, his face showing bemusement at the unexpected offer. They locked eyes for a long awkward beat, then adding to his surprise, the other boy nodded. A strange sensation started in his belly at the other boy's acceptance. Catching the attention of one of the cocktail waitresses, he offered the girl a few bills then ordered another Glencallan 18. He went to order the same for Humphrey, only to be surprised when the other boy cut in and ordered two fingers of Balmoor, albeit a much younger one, neat. He was reluctantly impressed, Humphrey knew decent whisky. What surprised him more, even though it probably shouldn't have, is that Humphrey paid for his own drink. He had offered, so he had expected to pay for the other boy's drink.

"You look surprised, did you honestly think I was going to accept a free drink from you?" He shrugged.

"Have it your way," He shrugged, "just trying to be nice since you're dating my soon to be sister." The look Humphrey sends his way is disbelieving but the other boy said nothing. They descended into an awkward, but not uncomfortable silence until Humphrey was knocked into by some guy who clearly couldn't hold his liquor. The guy turned, hopefully to apologize only to stop and leer at Humphrey.

"Let me guess, your name is Rocky." The guy said in a tone that Chuck recognized immediately, causing his stomach to tighten uncomfortably. "Because you would definitely be good for relieving my tension." He sent a dark look towards the drunk boy, even as he tried to convince himself that his anger was on Serena's behalf. Humphrey just sounded amused as he responded,

"Do I look blond and tan to you?"

"No, well then maybe I can be your Rocky?"

"Thanks but no, I've already got someone to relieve my tension." He thought that'd be the end of it, but the drunk, who also seemed to be an idiot, persisted.

"This guy?"He noticed the guy looking in his direction, "Doesn't look like he's doing a very good job." Definitely an idiot, he decided, glaring. Did this nobody not realize who he was? Was he really implying he couldn't satisfy Humphrey? He'd blow Humphrey's mind, even ruin him for others if he wanted - which he definitely didn't. Meanwhile Humphrey burst out laughing,

"Chuck? No, definitely not." He fought to keep his expression neutral, the same clenching sensation from earlier could be felt at this new reminder than Humphrey doesn't like him. No! He thought, annoyed with himself, he doesn't care if the other boy doesn't like him - more than that, he doesn't want the other boy to like him.

The idiot finally seemed to get the message when Serena came back, and wrapped her arms around Humphrey. She didn't even seem to notice the idiot as she whispered into her boyfriend's ear.

"No." Humphrey said, with a shake of his head.

"Please?" The blonde pouted, then leaned in and whispered some more, before... His stomach tightened uncomfortably. The entire scene was nauseating. He was about to excuse himself, though the couple really wasn't paying him any mind anyway, when Humphrey reluctantly nodded and allowed Serena to pull him away.

“Green really isn't your color.” He shot Blair an annoyed look once he realized what she meant. She sent her own unimpressed look back, and continued before he could speak. “Still insisting you don't have a thing for him?” She asked, with a quirk to her lips like she wasn't trying very hard to hide her smile.

"I'm not jealous of Humphrey." He scoffed, as he tried, without much success, to relax tense muscles.

“Not of him, Bass. You're jealous over him, there's a difference. Deny it all you want, but you're attracted to him and you can't stand that someone else gets to touch him when you can't." Blair smirked, then sighed, "Just go after him already.” He turned to her, his eyes shrewd.

“Your best friend sleeps with your boyfriend, so you send his best friend to sleep with her boyfriend?” He questioned, “Normally I'd see the poetic justice in that but there's one flaw to your plan. I don't want him, this new curiosity is just messing with my head. I'm sure once I take a guy to my bed, whatever this is will go away and Humphrey will go back to being beneath my notice.” He said, shoving the memory of the failed attempt at the gay club that tried to contradict this belief he was trying to cling to back to the furthest recesses of his mind.

“Hard though it may be to believe this isn't me being vindictive about Serena’s betrayal. This is me encouraging you to go after someone you obviously want. However, since you’re still managing to fool yourself with this denial act, I'll play along. If you want to sate your curiosity, then there are plenty of boys here for you to choose from.” Blair said, before taking a sip from her glass.

He nodded in agreement, casting his gaze casually over the room until his breath caught as he felt it. Subtle but there, that little flicker of interest he hadn't felt with any other guy. Well, except Humphrey; he really didn't understand what was going on with him. Ever since the..event he tried not to think about... he'd started checking out other boys as subtly as he could even going as far as actually attending gym a couple times and peeking in the boys locker room. Admittedly, that didn't help much since Humphrey was in his gym class and he inevitably found himself glancing at him. Still, none of the other boys affected him at all but the dreams featuring Humphrey continued. The one from last night came to him, unbidden. He shook the fantasy from his thoughts before it took hold, and turned his attention back to the guy who'd sparked this interest: one of the bartenders.

“Such good ideas you have.” He drained the rest of his scotch, and handed Blair the glass. She had apparently followed his gaze to figure out who had caught his attention because her next words were,

“Don't you steal one of my bartenders in the middle of my event! Chuck!” He approached the bar, paying no mind to Blair’s continued objections.

“You. What's your name?” He asked the guy.

“Greg.”

“Well Greg, Miss Waldorf has requested you head upstairs. She's opening the VIP bar.” He said, coming up with the lie on the spot. Once Greg left, Chuck ordered another drink and nursed it for a few minutes before draining it. He set the empty glass on the bar and slipped out the door toward the staircase leading to the VIP lounge. Once inside, he locked the door as Greg turned towards him.

“This bar isn't even set up to be opened. Miss Waldorf didn't request me.”

“True, I just said that to get you alone,” Chuck said, approaching the other man. “Do you mind?”

“I, well, no. But Miss Waldorf...I can't afford to lose this job.” Greg said, taking a seat on one of the lounge couches.

“Don't worry, if Blair's going to be angry with anyone it'll be me. Trust me, your job is safe.” Chuck promised, taking a seat next to him. When Greg nodded, he closed the distance between them.

XOXO

Chuck stared at the seven digits on his hand, lost in thought. Eventually Chuck got up, straightened his own clothes and made his way down stairs. He found a server and ordered another drink, then went and found a more secluded spot.

After a few minutes, a tumbler of Glencallen 18 appeared in front of him. He didn't bother looking up as he pulled his wallet out to tip the woman only for a familiar voice to stop him.

“Don't need or want your money Bass.” He finally looked up just in time to see Blair take the chair across from him.

“Since when do you do the job of the help?” He asked. He had an idea of what she wanted, and he wanted to avoid it as long as possible.

“Only when necessary.” She responded, he could feel her eyes on him, “I wanted to talk to you, and didn't want any distractions.”

“Let me guess… you want a detailed account of what I was doing. I don't usually kiss and tell, but I could make an exception for you.”

“No, thank you.” He smirked as her face scrunched up with disgust. “What I do want is for you to finally admit you want to sleep with Humphrey.”

“Why would I do that?” He asked, keeping his expression neutral. She couldn't possibly know what happened, she was just pushing the delusion she'd latched onto. Except it didn't seem so delusional now, given what had happened with Greg.

“Maybe because out of all of the guys you could have chosen, you went with the one that could be Humphrey's twin.”

**Notes for the Chapter:**

> Trivia
> 
> \- Bartender Greg actually comes from the book series where he's a character that both Chuck and Dan had a dalliance with. Unlike in the books though, Bartender Greg has not been with Dan. In fact, he bears a striking resemblance to Dan here, further proving to Blair that she's right about Chuck having a thing for Dan.


End file.
